2-Hydroxymethyl-5-(6-methyl-purin-9-yl)-tetrahydro-furan-3,4-diol

ID: ALA1269736

Chembl Id: CHEMBL1269736

Cas Number: 14675-48-0

PubChem CID: 97131

Max Phase: Preclinical

Molecular Formula: C11H14N4O4

Molecular Weight: 266.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C11H14N4O4/c1-5-7-10(13-3-12-5)15(4-14-7)11-9(18)8(17)6(2-16)19-11/h3-4,6,8-9,11,16-18H,2H2,1H3/t6-,8-,9-,11-/m1/s1

Standard InChI Key:  FIGBCBGMUIGJBD-PNHWDRBUSA-N

Alternative Forms

1. Parent:

   

   ALA1269736

   (2R,3S,4R,5R)-2-(Hydroxymethyl)-5-(6-methyl-9H-purin-9-yl)tetrahydrofuran-3,4-diol

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 266.26

Molecular Weight (Monoisotopic): 266.1015

AlogP: -1.25

#Rotatable Bonds: 2

Polar Surface Area: 113.52

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 2.96

CX LogP: -1.73

CX LogD: -1.73

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.62

Np Likeness Score: 1.08

References

1. Kusachi S, Thompson RD, Bugni WJ, Yamada N, Olsson RA..  (1985)  Dog coronary artery adenosine receptor: structure of the N6-alkyl subregion.,  28  (11): [PMID:2999397] [10.1021/jm00149a016]

2. Van Aerschot AA, Mamos P, Weyns NJ, Ikeda S, De Clercq E, Herdewijn PA..  (1993)  Antiviral activity of C-alkylated purine nucleosides obtained by cross-coupling with tetraalkyltin reagents.,  36  (20): [PMID:8411010] [10.1021/jm00072a013]

3. Wu R, Smidansky ED, Oh HS, Takhampunya R, Padmanabhan R, Cameron CE, Peterson BR..  (2010)  Synthesis of a 6-methyl-7-deaza analogue of adenosine that potently inhibits replication of polio and dengue viruses.,  53  (22): [PMID:20964406] [10.1021/jm100593s]

4. Hassan AE, Abou-Elkhair RA, Riordan JM, Allan PW, Parker WB, Khare R, Waud WR, Montgomery JA, Secrist JA..  (2012)  Synthesis and evaluation of the substrate activity of C-6 substituted purine ribosides with E. coli purine nucleoside phosphorylase: palladium mediated cross-coupling of organozinc halides with 6-chloropurine nucleosides.,  47  [PMID:22112758] [10.1016/j.ejmech.2011.10.039]

5. Hassan AE, Abou-Elkhair RA, Parker WB, Allan PW, Secrist JA..  (2016)  6-Methylpurine derived sugar modified nucleosides: Synthesis and in vivo antitumor activity in D54 tumor expressing M64V-Escherichia coli purine nucleoside phosphorylase.,  108  [PMID:26724729] [10.1016/j.ejmech.2015.12.029]

Source

Source(1):

• Scientific Literature